Chemische Berichte · 1991 · 46 citations · 24 references
Denticulatins 1Bioorganic ChemistryChiral AllylboronatesEngineeringNatural SciencesDiversity-oriented SynthesisTotal SynthesisOrganic ChemistryStereoselective SynthesisPharmacologyAsymmetric CatalysisSynthetic ChemistryEnantioselective SynthesisBiomolecular EngineeringNatural Product Synthesis
Abstract The total synthesis of the denticulatins 1 is described. Key feature is the efficient generation of the C‐1‐to‐C‐9 building block 37 by three consecutive stereoselective carbon ‐ carbon bond‐forming steps using chiral allylboronates. The C‐10‐to‐C‐17 building block was obtained by kinetic Sharpless resolution of an allylic alcohol followed by an Ireland‐Claisen rearrangement.
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